Osmium tetraoxide cis hydroxylation of unsaturated substrates

Schroeder, M.

doi:10.1021/cr60324a003

Cited by 603 publications

(247 citation statements)

References 42 publications

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“…12 PE and PP are inert toward OsO 4 staining, but OsO 4 reacts with unsaturated C-C double bonds via dihydroxylation. 10,13 As outlined in Figure 1e, we in-fill separator samples with butter, 7 The binary data set for the PE16A separator is available open source 14 and contains data corresponding to a separator volume of 12 × 7 × 5 μm 3 . Figure 2a presents a rendered sub-volume with an edge length of 2 μm (<1/50th of the total imaged volume).…”

Section: Methodsmentioning

confidence: 99%

Communication—Technique for Visualization and Quantification of Lithium-Ion Battery Separator Microstructure

Lagadec

Ebner

Zahn

et al. 2016

J. Electrochem. Soc.

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Separators play an important role in lithium-ion battery operation; however, no comprehensive studies of their microstructure and its impact exist. To enable such studies, we present a simple method for separator microstructure visualization and quantification based on focused-ion-beam scanning electron microscopic tomography. Here, we use this approach to visualize a sample of commercial polyethylene separator, calculate its directional effective transport parameters, and explain the impact of these values on battery performance. We further extend this technique to visualize metallic deposition within the separator, which could facilitate the study of lithium plating and dendritic growth. Separators in Li-ion batteries (LIBs) prevent electronic contact between positive and negative electrodes while allowing ionic transport between them.1 In the event of cell failure, separators limit ion transport to avoid internal short-circuiting and thermal runaway.2 To achieve good transport and suitable mechanical, thermal, and chemical properties, LIB separators are commonly <25 μm-thick sheets consisting of a complex 3D structure featuring 40% porosity and submicron pore sizes.2 Though they are routinely characterized by thickness, pore size, porosity, as well as thermal and electrical properties, 3 there has been no quantitative measurement of their 3D structure. Microstructural data would be particularly helpful in light of recent studies that link separator structure to the likelihood of LIB failure (e.g., through Li dendrite growth 4 ) and changes in separator structure (e.g., through pore closure by mechanical stress and chemical degradation 5,6 ) to aging effects in LIBs. Here, we present a simple procedure for visualizing and quantifying separator microstructures. We use simulations to assess the implications of separator microstructure on battery performance and extend our technique to examine lithium metal deposition within the separator. ExperimentalWe employ focused ion beam scanning electron microscopic (FIB-SEM) tomography ( Figure S1 in the Supplementary Information 7 ), a technique that has been used for visualizing and quantifying of LIB electrode microstructures. 8,9 Figures 1a-1b show top view SEM images of polyethylene (PE) and polypropylene (PP) separators from Targray (PE16A and PP16). SEM images of cross-sectional cuts through the same separators (Figures 1c-1d) taken in the FIB-SEM configuration show pore edge contrast and depth information from the pores. Because these effects complicate image processing and quantification of the 3D microstructure, we in-fill the separator to enable imaging of a planar surface.Quantification of the 3D microstructure also requires sufficient contrast between the polymer skeleton and the in-filled pores. As a staining agent, we use OsO 4 , 10 which has previously been used with Celgard microporous membranes 11 as well as lithium dendrites and solid electrolyte interphases of graphite electrodes.12 PE and PP are inert toward OsO 4 staining, but OsO 4 reacts with unsa...

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Section: Methodsmentioning

confidence: 99%

Communication—Technique for Visualization and Quantification of Lithium-Ion Battery Separator Microstructure

Lagadec

Ebner

Zahn

et al. 2016

J. Electrochem. Soc.

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“…It is industrially important both in biological chemistry for the "fixation" of biological tissue and in medicine [6]. Another application of this compound is in the fine organic chemicals industry because it can be used stoichiometrically or catalytically in the cis-dihydroxylation of alkenes to cis-diols [7,8]. A very wide range of alkenes and unsaturated organic substrates has been oxidized using OsO 4 .…”

Section: Introductionmentioning

confidence: 99%

A comparative study of DFT and traditional ab initio methodologies on the OsO4 molecule

Ujaque

Maseras

Lleds

2000

Int. J. Quant. Chem.

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ABSTRACT:The performance of different conventional ab initio methodologies and density functional procedures is compared through its application to the theoretical calculation of the bond distance and harmonic vibrational frequencies of the OsO 4 molecule. The problem of the basis set is first considered, with up to nine different basis sets being tested in calculations using the hybrid Becke3LYP density functional, and the most appropriate basis set is used in the comparison of Hartree-Fock, post-Hartree-Fock, and density functional methods. The post-Hartree-Fock methods analyzed are MP2, CISD, and CCSD(T), and the density functionals tested are SVWN, BLYP, BPW91, and Becke3LYP. The results show that for this particular system density functional methods perform better than do HF-based methods with the exception of CCSD(T), which gives the best overall results.

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“…Osmium tetroxide probes of DNA structure have a number of advantages as compared to enzymatic and other chemical probes [4,5,16]; among these is the established chemistry of their interaction with DNA components (for review, see [18]), detection of the osmium binding sites at single nucleotide resolution [5,[19][20][21][22][23], availability of antibodies against osmiummodified DNAs [5,24], etc. Os,TMEN represents a second osmium probe which can be applied to probe DNA structure in situ.…”

Section: Discussionmentioning

confidence: 99%

Osmium tetroxide, N,N,N',N'‐tetramethylethylendiamine A new probe of DNA structure in the cell

Boublíková

Paleček

1990

FEBS Letters

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Osmium tetraoxide cis hydroxylation of unsaturated substrates

Cited by 603 publications

References 42 publications

Communication—Technique for Visualization and Quantification of Lithium-Ion Battery Separator Microstructure

Communication—Technique for Visualization and Quantification of Lithium-Ion Battery Separator Microstructure

A comparative study of DFT and traditional ab initio methodologies on the OsO4 molecule

Osmium tetroxide, N,N,N',N'‐tetramethylethylendiamine A new probe of DNA structure in the cell

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